Literature DB >> 15755144

A new synthetic method for alpha-alkoxycarbonyl iminium salt and its reaction with nucleophiles.

Makoto Shimizu1, Hiroyuki Itou, Megumi Miura.   

Abstract

An iminium salt was easily prepared using the oxidation of amino ketene silyl acetal with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, and the subsequent nucleophilic addition to this iminium species proceeded efficiently to afford alpha-amino esters in good yields.

Entities:  

Year:  2005        PMID： 15755144     DOI： 10.1021/ja042330f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone.

Authors:  Makoto Shimizu; Hayao Imazato; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-06-03       Impact factor: 4.036

2.  Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors:  Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-07-29       Impact factor: 4.036

3.  N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction.

Authors:  Makoto Shimizu; Asako Higashino; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2021-04-07       Impact factor: 3.361

4.  An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.

Authors:  Makoto Shimizu; Takayoshi Morimoto; Yusuke Yanagi; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

5.  Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether.

Authors:  Makoto Shimizu; Shingo Hata; Koichi Kondo; Kazuhiro Murakami; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-07-24       Impact factor: 4.036

6.  Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors:  Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal:  Chem Sci       Date:  2018-05-16       Impact factor: 9.825
  6 in total

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